新型含氟植物生长调节剂——取代4,4,4-三氟-3-(吲哚-3-基)丁酸的合成及其生物活性

Synthesis and Biological Activities of Substituted 4,4,4-Trifluoro-3-(indoIe-3-)butyric Acids, Novel Fluorinated Plant Growth Regulators.

作者信息

Katayama M, Gautam R K

机构信息

a Laboratory of Bioorganic Chemistry, Department of Chemistry , National Industrial Research Institute of Nagoya , 1-1 Hirate-cho, Kita-ku, Nagoya 462 , Japan.

出版信息

Biosci Biotechnol Biochem. 1996 Jan;60(5):755-9. doi: 10.1271/bbb.60.755.

DOI:10.1271/bbb.60.755

PMID:27281137

Abstract

Substituted 4,4,4-trifluoro-3-(indole-3-)butyric acids (TFIBAs), novel fluorinated plant growth regulators, were easily synthesized from substituted 2,2,2-trifluoro-l-(indole-3-)ethanols. The synthetic substituted TFIBAs showed marked root growth-promoting activity toward Chinese cabbage, lettuce, and rice plants. 5-MeO-2-Me-TFIBA (2d) had especially strong promoting activity toward Chinese cabbage, while 5-Me- TFIBA (2b) markedly promoted the root growth of all three plants. The promoting activity of TFIBAs halogenated at the 5-position in the indole nucleus of the molecule (5-Br- and 5-C1-TFIBA (2e and 2g)) was also greater than the activity of TFIBA, the original non-substituted compound. 5-N02-TFIBA (2h) with a strong electron-withdrawing group showed only very weak root growth-promoting activity.

摘要

取代的4,4,4-三氟-3-(吲哚-3-基)丁酸(TFIBAs)是新型的氟化植物生长调节剂，可由取代的2,2,2-三氟-1-(吲哚-3-基)乙醇轻松合成。合成的取代TFIBAs对大白菜、生菜和水稻植株表现出显著的促根活性。5-甲氧基-2-甲基-TFIBAs(2d)对大白菜具有特别强的促进活性，而5-甲基-TFIBAs(2b)显著促进了所有三种植物的根系生长。分子吲哚核5位卤代的TFIBAs(5-溴-和5-氯-TFIBAs(2e和2g))的促进活性也高于原始未取代化合物TFIBA的活性。带有强吸电子基团的5-硝基-TFIBAs(2h)仅表现出非常弱的促根活性。